Too Late to Book a Holiday Getaway? Not Necessarily

Catching a wave in San Juan, P.R.Credit
Laura Magruder for The New York Times

We’re into December, when last-minute planners from New York and other scarf-wearing regions start dreaming of spending Christmas break on a Caribbean beach somewhere, anywhere. Or, to put it more accurately, dream of having had the foresight to plan such a trip in August, when prices — both flights and hotel rooms — were still reasonable. Conventional wisdom has it that booking now for a late December getaway is a fool’s errand, and a rich fool at that.

But is it? Could someone who was flexible on destinations and dates still pull off a reasonably priced getaway around Christmas and New Year’s? Or would they be better off reserving now for later in the winter?

I decided to look into these matters with some good old-fashioned research. Well, not too old-fashioned: I used Google’s “Explore Flights” page, an amazing site that lets you set a few criteria — what region you want to visit, how many days you want to go for, acceptable departure times and flight lengths — and then spits out a list of destinations with a day-by-day bar graph of the best airfares. (I found that they were occasionally inaccurate, especially with JetBlue flights, but the errors were within a $50 margin and always overestimated the cost.)

Unfortunately, no such tool works the same magic for lodging. So I decided I’d do standard searches on Booking.com, whose ratings I trust more than TripAdvisor since they claim to allow only users who have booked and paid for the hotel to review it. Here were my minimum criteria:

4) And four nights in a hotel (or guesthouse or hostel with private rooms) with a minimum Booking.com rating of 7.5 (in the midrange of the site’s “Good” level)

The idea was not to find and recommend specific itineraries. Instead I wanted to answer some questions: What, if anything, was still available? Are certain travel days better than others? And how would you save if you booked a similar trip now for later in the winter?

So on Tuesday afternoon and Wednesday morning of this week I searched 12 classically beachy locales in and around the Caribbean, including budget destinations like Montego Bay, Jamaica; Punta Cana, Dominican Republic; and Cancún, Mexico; slightly more upscale spots like San Juan, P.R., and Key West, Fla., ; as well as Panama, as a wild card. It was exhausting, but hardly exhaustive — I may not have found all the best deals, nor was my 7.5 rating requirement the way I would typically decide on lodging. But enough caveats. Here are my findings.

Flights

The cheapest round-trip flights are after pre-Christmas weekend rush to get out of town but before Christmas Day — in other words, Monday, Dec. 23, and Tuesday, Christmas Eve. (The only exceptions I found: San Juan, where leaving Saturday, Dec. 21, was the cheapest available, at $447, and Antigua, where traveling on Christmas Day was cheapest, at $880.) Traveling on the cheapest days meant a 30 to 50 percent savings over traveling on the most expensive, which were mostly for trips that included New Year’s.

That was not a shock, although I had expected traveling on Christmas Day would have been cheapest in more than just one instance. What surprised me more was that some of those cheaper flights were not much more expensive than ones to the same destinations more than two months out for midwinter break, the week starting Feb. 15. Sometimes, in fact, it was cheaper: You could get to Nassau in the Bahamas over Christmas for $422, but the lowest flight over February break was $476.

Still, anyone willing to travel during non-holiday or non-break stretches of January and February could save quite a bit. A few examples of the biggest differences: The best rate over Christmas for St. Thomas is $649, but that dips to $335 on some other winter dates; for Aruba, it’s $622 versus $396; Cancún, $685 versus $365; and for Barbados, a whopping $913 versus $486. (Get your Bajan food in Brooklyn this year.)

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Unlike flights, hotel prices followed no obvious pattern and tended to complicate things. That $649 flight to St. Thomas made Dec. 23 look like the best day to leave for the Virgin Islands, until I saw that the cheapest available hotel on Booking.com with a rating of over 7.5 for those dates was over $600 a night. Abort!

Other times, cheaper flight days matched cheaper hotel days. I was able to match a $685 flight to Cancún on Dec. 24 with a $66-a-night room at the Hotel Suites Gaby. But flying on Dec. 26 (for $1,203) the cheapest available hotel was over $600 a night. And unlike with flights, you could save big on lodging — 17 to 64 percent over holiday-time lows — if you book now for that February vacation week (and sometimes even more if you’re open to other dates).

The overall cheapest four-night getaway I found was to San Juan, from Dec. 21 to 25, traveling nonstop on JetBlue for $447 (where I can assure you free snacks will be served) and staying for $78 a night at the Casa Del Caribe Bed & Breakfast (where I’ve never been, though it got a 7.8 rating on Booking.com). Grand total for two: $1,206. A Montego Bay combo was second at $1,558, and St. Maarten third at $1,836.

But cheapest doesn’t mean the best deal — or, I suppose, the least bad deal. So I also calculated which trips suffered the least markup for a Christmas trip when compared with flexible winter dates. Key West was the winner here — though not cheap: A trip from Dec. 23 to 27 was only 12 percent more ($2,059 total) than open winter dates ($1,844), and almost the same as the cheapest four-day stretch of February break. All other destinations were at least a 30 percent markup. And some scenarios really argued for waiting until after the holidays: The best I could do for a couple in Aruba over Christmas was $2,060 for four days, an 89 percent markup over heading there from Feb. 3 to 7 for a reasonable $1,092.

I’d also note that while it may not be quite as tranquil nor toasty a getaway, you can still get down to Miami Beach over the holiday more cheaply than any place mentioned above. There were plenty of flights for under $500 (compared with $250 or so later in winter). Average high should be in the mid-70s — not bad for the price tag.

Do It Yourself

Here’s how I went about finding the best deals — and some advice if you decide to take the plunge.

1) Set aside a couple of hours.

2) Using Google’s “Explore Flights” service, plug in your requirements: beach region of choice, as well as trip length, travel time (13-hour, two-layover trips are not worth it for a few days) and maybe departure and arrival times if you want to avoid middle-of-the-night flights, common on JetBlue. Jot down the cheapest couple of dates for a few places you’d be excited to visit.

3) Match that list with the lodging search of your choice. If you go with Booking.com, be sure to actually read the reviews and check the hotel’s website — steps that I didn’t take. Or choose another booking site, dive into TripAdvisor reviews, scrounge for remaining private rentals on Airbnb.com or check what hostels still have beds. Resort-lovers may want to check package deals at sites like cheapcaribbean.com, though when I did a few searches for the Christmas period nothing beat my other method.

4) Total up flight and lodging, estimate additional costs and see if any of the options strike you as doable.

5) Now choose an acceptable set of dates later in the winter and do the process over again.

6) Weigh the lower cost of delayed gratification against the urgency of fleeing the cold posthaste. Consider whether spending a chunk of the savings on, say, a daily infusion of upscale hot chocolate would make sticking around for the holidays any more bearable.